rac-(E)-4-Hepten-2-ol | 58927-81-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: rac-(E)-4-Hepten-2-ol
• 英文别名: (E)-hept-4-en-2-ol；(E)-4-Hepten-2-ol；trans-4-Hepten-2-ol；(+/-)-(4E)-4-hepten-2-ol；hept-4t-en-2-ol；4-Hepten-2-ol, (4E)-
• CAS: 58927-81-4
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: KZUFTCBJDQXWOJ-SNAWJCMRSA-N

物化性质

• 熔点：
  26°C (estimate)
• 沸点：
  178.73°C (estimate)
• 密度：
  0.8596 (estimate)
• LogP：
  2.051 (est)
• 保留指数：
  863;863

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  rac-(E)-4-Hepten-2-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以49%的产率得到(4E)-4-庚烯-2-酮
  参考文献：
  名称：

  Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications

  摘要：

  Extracts from different body parts of adult female Eriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols with S-configuration was attractive to male E. sparrmannella (Bosc), whereas no males of E. cicatricella were found in these traps. The sex pheromone compounds in E. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.

  DOI：

  10.1007/bf02033660
• 作为产物：
  描述：

  2,4-庚二烯-6-酮 在 lithium aluminium tetrahydride 作用下， 生成 rac-(E)-4-Hepten-2-ol
  参考文献：
  名称：

  Chantegrel,B.; Gelin,S., Bulletin de la Societe Chimique de France, 1975, p. 2639 - 2642

  摘要：

  DOI：

文献信息

• In situ 1H-PHIP-NMR studies of the stereoselective hydrogenation of alkynes to ( E)-alkenes catalyzed by a homogeneous [Cp*Ru]+ catalyst
  作者：Dana Schleyer、Heiko G. Niessen、Joachim Bargon

  DOI：10.1039/b007201j

  日期：——

  The hydrogenation of internal alkynes using a [Cp*Ru(alkene)]+ complex leads to the formation of (E)-alkenes. This ruthenium complex represents one of the few homogeneous catalysts that trans-hydrogenate internal alkynes directly and stereoselectively. We have studied its stereoselectivity by in situ PHIP-NMR spectroscopy (PHIP = para-hydrogen induced polarization). With this method the initially formed products can be identified and characterized even at very low concentrations and low conversions. Furthermore, their subsequent fate can be evaluated with high sensitivity and with time resolution. Different alkyne substrates were used to demonstrate the universal applicability of this catalyst. The catalyst is not active in combination with terminal alkynes, however, possibly due to the formation of a rather stable vinylidene complex. A mechanism proceeding ia a binuclear complex is proposed to explain the formation of the (E)-alkenes.

  使用[Cp*Ru(烯烃)]+复合物对内炔进行氢化反应，生成(E)-烯烃。这种钌复合物是少数能够直接且选择性地进行反式氢化内炔的均相催化剂之一。我们通过原位PHIP-NMR光谱学（PHIP=邻氢诱导极化）研究了其选择性。利用这种方法，即便在极低的浓度和转化率下，初始生成的产物也能被识别和表征。此外，其后续变化可以高灵敏度和时间分辨率进行评估。采用不同的炔烃底物来展示这种催化剂的广泛适用性。然而，该催化剂在与端炔结合时并不活跃，可能是因为生成了相对稳定的亚乙烯基复合物。为了解释(E)-烯烃的生成，我们提出了一种通过双核复合物的反应机理。
• [EN] 4-HEPTEN-2-YL SALICYLATE AND ITS USE AS FRAGRANCE INGREDIENT<br/>[FR] 4-HEPTENE-2-YLE SALICYLATE ET SON UTILISATION COMME AGENT PARFUMANT
  申请人：GIVAUDAN SA

  公开号：WO2006007755A1

  公开（公告）日：2006-01-26

  The present invention is related to 4-hepten-2-yl salicylate and its use as fragrance ingredient.

  本发明涉及4-庚烯-2-基水杨酸酯及其作为香料成分的用途。
• New Volatile Sulfur-Containing Constituents in a Simultaneous Distillation−Extraction Extract of Red Bell Peppers (Capsicum annuum)
  作者：Regula Naef、Alain Velluz、Alain Jaquier

  DOI：10.1021/jf072493y

  日期：2008.1.1

  mercapto-alcohols 17, 18, and 30, the dithiols 19 and 28, the methylthio-thiols 20 and 21, and the thiophene-thiol 31) and the two new dithiolanes 10 and 29. All of them are structurally related to the unsaturated C7- and C9-ketones 1- 4. The free thiols were enriched using Affi-Gel 501 ( p-aminophenyl-mercuric acetate grafted on an agarose gel). The new compounds were confirmed by syntheses and were organoleptically

  通过同时蒸馏-萃取（SDE，Likens-Nickerson）制备红甜椒（Capsicum annuum）的提取物。除了已知的（3 E）-3-庚-2-酮（1）外，不饱和C9-酮1-壬烯-4-酮（2），（2 E）-2-壬烯-4-酮（3）和（2 E，5 E）-2,5-nonadien-4-one（4），2-甲氧基-3-异丁基吡嗪（5）和庚烷-2-硫醇（6），我们确定了19新硫醇（脂族饱和和不饱和硫醇14-16和22-27，巯基酮12和13，巯基醇17、18和30，二硫醇19和28，甲硫醇20和21 ，以及噻吩-硫醇31）和两个新的二噻吩10和29。它们在结构上均与不饱和C7-和C9-酮1-4相关。使用Affi-Gel 501（对氨基苯酚）富集了游离硫醇-乙酸汞接枝在琼脂糖凝胶上）。
• [EN] CYCLOPROPANATION PROCESS<br/>[FR] PROCÉDÉ DE CYCLOPROPANATION
  申请人：GIVAUDAN SA

  公开号：WO2009023980A1

  公开（公告）日：2009-02-26

  A method for the preparation of cyclopropyl carbinols by cyclopropanation of unsaturated alcoholates, utilising a reagent system selected from (A) magnesium metal and dibromomethane, and (B) dibromomethane and a tertiary Grignard reagent, the reaction being carried out in the presence of an ether solvent. The process is useful, for example, for the preparation of ingredients for the flavour and fragrance industry.

  一种通过使用选自(A)镁金属和二溴甲烷，以及(B)二溴甲烷和三级格氏试剂的试剂体系，通过环丙烷化不饱和醇酸盐来制备环丙基醇的方法，该反应在醚溶剂存在下进行。该过程可用于为香料和香精行业的成分制备。
• Palladium-Catalyzed Enantioselective Heck Alkenylation of Acyclic Alkenols Using a Redox-Relay Strategy
  作者：Harshkumar H. Patel、Matthew S. Sigman

  DOI：10.1021/ja5130836

  日期：2015.3.18

  carbonyl group in high enantioselectivity. The success of this reaction is attributed to the use of electron-withdrawing alkenyl triflates, which offer selective β-hydride elimination followed by migration of the catalyst through the alkyl chain to give the alkenylated carbonyl products. The synthetic utility of the process is demonstrated by a two-step modification of a reaction product to yield a tricyclic

  我们报告了烯基三氟甲磺酸酯和无环一级或外消旋二级烯醇的高度对映选择性分子间 Heck 反应。温和的反应条件允许在 β、γ 或 δ 位上以高对映选择性将广泛的烯基安装到羰基上。该反应的成功归功于吸电子烯基三氟甲磺酸酯的使用，它提供选择性的β-氢化物消除，然后催化剂通过烷基链迁移，得到烯基化的羰基产物。该方法的合成效用通过对反应产物进行两步修饰以产生存在于各种天然产物中的三环核心结构来证明。